Oxoammonium salt/NaClO2: an expedient, catalytic system for one-pot oxidation of primary alcohols to carboxylic acids with broad substrate applicability

Abstract

A facile, green, one-pot oxidation of primary alcohols to carboxylic acids with broad substrate applicability has been developed by employing an expedient catalytic system consisting of 1-Me-AZADO+X-/NaClO2.

Discovery and Exploitation of AZADO: The Highly Active Catalyst for Alcohol Oxidation

“…NaOCl/NaClO 2 (Merck's method) failed to afford a carboxylic acid product in good yield due to damage to the electron-rich functionalities. In addition to the superiority of 1-Me-AZADO over TEMPO, it should be noted that direct investment of the substantial catalyst, the oxoammonium salt, brought about a marked productivity 56) ( Table 9). The scope of the oxoammonium salt/NaClO 2 method for the one-pot oxidation of primary alcohols to carboxylic acids is shown in attained by 1-Me-AZADO + should be attributed to the highly reactive nature of 1-Me-AZADOH in consuming NaClO, quenching the destructive pathway of reacting π-electrons of the substrates.…”

Efficient Total Synthesis of Bongkrekic Acid and Apoptosis Inhibitory Activity of Its Analogues

“…Careful extraction from an aqueous solution at pH 5 after quenchingwith isopropanolwas essential for areproducible yield because more acidic conditions (pH 1) duringe xtraction caused decompositiono ft he product. Finally,w es uccess- [30] Because of its instability and high polarity,B KA must be carefully purified and the side products should be removed from MOM ester 49 by columnchromatography at this stage. The purified MOM ester 49 could be deprotected with 6 m HCl in THF without the formation of geometrical isomers.…”

3‐Methyl‐4‐oxa‐5‐azahomoadamantane: Alkoxyamine‐Type Organocatalyst for Alcohol Oxidation

“…[12] In contrast, the oxidative dimerization and spontaneous isomerization proceeded under one-electron oxidation conditions to give the diazo compound 9 in high yield (Scheme 5 b). We conducted a large-scale oxidation of isopropyl alcohol (20 mmol) with 0.6 equivalent of NaOCl and obtained the residue after extraction and evaporation.…”

“…Notably, a similar oxidative transformation of 1 into the oxoammonium salt 11 proceeded in 67 % yield using NaOCl in the presence of HClO 4 (Scheme 5 a). [12] In contrast, the oxidative dimerization and spontaneous isomerization proceeded under one-electron oxidation conditions to give the diazo compound 9 in high yield (Scheme 5 b).…”